Diisopropylamine → 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(5-hydroxypent-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	4-Pentyn-1-ol	HCID 79346	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	2-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one	HCID 59790307	—
Catalyst	Bis(benzonitrile)palladium chloride	HCID 498840	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(5-hydroxypent-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one	HCID 59790323	73.3%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1.15 g, 2.8 mmol), dioxane, bis(benzonitrile)dichloropalladium(II) (32.2 mg, 0.084 mmol), tri-tert-butyl phosphine (10% w/w in hexane, 339 mg, 0.17 mmol) and diisopropyl amine (340 mg, 3.36 mmol) was degassed under argon for 5 minutes, treated with pent-4-yn-1-ol (236 mg, 2.8 mmol), stirred at 80° C. for 5 hours, poured into water and extracted with ethyl acetate. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by ICSO (EtOAc/MeOH 10/1) gave the title compound as a white solid (849 mg), identified by NMR and mass spectral analyses. MS m/e [M+H]+ 414.2

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07423158B2
Source dataset	uspto-grants-2008_09
ORD ID	ord-5415d204dca748d18d663fed98bde097
Source note	uspto-grants-2008_09